Triclinic, P1 a = (2) Å b = (3) Å c = (4) Å = (1) = (1) = (1) Data collection.
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1 organic compounds Acta Crystallographica Section E Structure Reports Online ISSN Benzyl N 0 -(4,6-dimethoxy-2-methyl-3- phenyl-1h-indol-7-ylmethylene)- hydrazinecarbodithioate Hamid Khaldei, Hapipah Mohd Ali and Seik Weng Ng* Department of Chemistry, University of Malaya, Kuala Lumpur, Malaysia Correspondence seikweng@um.edu.my Received 15 November 2008; accepted 19 November 2008 Key indicators: single-crystal X-ray study; T = 100 K; mean (C C) = Å; R factor = 0.048; wr factor = 0.146; data-to-parameter ratio = The asymmetric unit of the title compound, C 26 H 25 N 3 O 2 S 2, contains two independent molecules, which are linked by a pair of N HS hydrogen bonds, forming a dimer. Related literature For a list of references of the benzyl esters of hydrazinecarbodithioic acids, see: Khaledi et al. (2008). For further synthetic details, see: Ali & Tarafder (1977); Jones et al. (2005). Triclinic, P1 a = (2) Å b = (3) Å c = (4) Å = (1) = (1) = (1) Data collection Bruker SMART APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T min = 0.906, T max = Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections Table 1 Hydrogen-bond geometry (Å, ). V = (9) Å 3 Z =4 Mo K radiation = 0.25 mm 1 T = 100 (2) K mm measured reflections independent reflections 7429 reflections with I > 2(I) R int = parameters H-atom parameters constrained max = 0.38 e Å 3 min = 0.33 e Å 3 D HA D H HA DA D HA N1 H1S (2) 164 N4 H4S (2) 170 Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X- SEED (Barbour, 2001); software used to prepare material for publication: pubcif (Westrip, 2008). We thank the University of Malaya for funding this study (Science Fund grants , ). Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2850). Experimental Crystal data C 26 H 25 N 3 O 2 S 2 M r = References Ali, M. A. & Tarafder, M. T. H. (1977). J. Inorg. Nucl. Chem. 39, Barbour, L. J. (2001). J. Supramol. Chem. 1, Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Jones, A. W., Wahyuningsih, T. W., Pchalek, K., Kumar, N. & Black, D. S. C. (2005). Tetrahedron, Khaledi, H., Ali, H. M. & Ng, S. W. (2008). Acta Cryst. E64, o2430. Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, Westrip, S. P. (2008). publcif. In preparation. o2442 Khaldei et al. doi: /s
2 supporting information [doi: /s ] Benzyl N -(4,6-dimethoxy-2-methyl-3-phenyl-1H-indol-7-ylmethylene)hydrazinecarbodithioate Hamid Khaldei, Hapipah Mohd Ali and Seik Weng Ng S1. Comment For a list of references of the benzyl esters of hydrazinecarbodithioic acids, see: Khaledi et al. (2008). For further synthetic details, see: Ali & Tarafder (1977); Jones et al. (2005). S2. Experimental 4,6-Dimethoxy-2-methyl-3-phenylindole-7-carbaldehyde was prepared by using a literature method (Jones et al., 2005) as was S-benzyl dithiocarbazate (Ali & Tarafder, 1977). 4,6-Dimethoxy-2-methyl-3-phenylindole-7-carbaldehyde (0.59 g, 2 mmol) and S-benzyl dithiocarbazate (0.40 g, 2 mmol) were refluxed in ethanol (40 ml) for 6 h. About 1 ml acetic acid was also added. The precipitate was filtered, washed with cold ethanol and dried. Yellow prisms of (I) were grown by slow evaporation of a DMF solution at room temperature S3. Refinement Hydrogen atoms were placed at calculated positions (C H = , N H = 0.88Å) and refined as riding with U(H) = times U eq (C,N). Figure 1 The molecular structure of (I) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Dashed lines denote hydrogen bonds. sup-1
3 Benzyl N -(4,6-dimethoxy-2-methyl-3-phenyl-1H- indol-7-ylmethylene)hydrazinecarbodithioate Crystal data C 26 H 25 N 3 O 2 S 2 M r = Triclinic, P1 Hall symbol: -P 1 a = (2) Å b = (3) Å c = (4) Å α = (1) β = (1) γ = (1) V = (9) Å 3 Data collection Bruker SMART APEX CCD diffractometer Radiation source: fine-focus sealed tube Graphite monochromator ω scans Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T min = 0.906, T max = Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 601 parameters 0 restraints Primary atom site location: structure-invariant direct methods Z = 4 F(000) = 1000 D x = Mg m 3 Mo Kα radiation, λ = Å Cell parameters from 3627 reflections θ = µ = 0.25 mm 1 T = 100 K Prism, yellow mm measured reflections independent reflections 7429 reflections with I > 2σ(I) R int = θ max = 27.5, θ min = 1.1 h = k = l = Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ 2 (F o2 ) + (0.0761P) 2 ] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max = Δρ max = 0.38 e Å 3 Δρ min = 0.33 e Å 3 Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq S (6) (4) (3) (14) S (6) (4) (3) (14) S (6) (4) (3) (15) S (6) (5) (3) (15) N (18) (14) (10) (4) H * N (19) (14) (10) (4) sup-2
4 N (18) (13) (9) (4) H * N (19) (14) (10) (4) H * N (19) (14) (9) (4) N (18) (13) (9) (4) H * O (16) (12) (8) (4) O (15) (12) (8) (3) O (16) (12) (8) (4) O (15) (12) (8) (3) C (2) (18) (13) (5) C (3) (19) (14) (6) H * C (3) (2) (15) (6) H3A * C (3) (2) (16) (7) H4A * C (3) (2) (16) (7) H * C (2) (19) (14) (6) H6A * C (2) (17) (13) (5) H7A * H7B * C (2) (17) (11) (5) C (2) (17) (12) (5) H * C (2) (17) (11) (4) C (2) (17) (12) (5) C (2) (17) (11) (5) H * C (2) (17) (11) (5) C (2) (16) (11) (4) C (2) (16) (11) (4) C (2) (16) (11) (4) C (2) (17) (12) (5) H17A * H17B * H17C * C (2) (16) (11) (4) C (2) (17) (11) (5) C (2) (17) (12) (5) H * C (2) (19) (12) (5) H * C (3) (19) (13) (6) H * sup-3
5 C (2) (18) (12) (5) H * C (2) (17) (12) (5) H * C (2) (17) (13) (5) H25A * H25B * H25C * C (2) (17) (12) (5) H26A * H26B * H26C * C (2) (18) (13) (5) C (3) (2) (16) (8) H * C (4) (2) (18) (10) H * C (3) (2) (16) (7) H * C (3) (2) (15) (6) H * C (3) (2) (14) (6) H * C (2) (18) (13) (5) H33A * H33B * C (2) (17) (12) (5) C (2) (16) (11) (5) C (2) (17) (11) (5) H * C (2) (17) (12) (5) C (2) (17) (12) (5) H * C (2) (17) (11) (4) C (2) (16) (11) (4) C (2) (16) (11) (4) C (2) (16) (12) (5) C (2) (17) (12) (5) H43A * H43B * H43C * C (2) (16) (11) (4) C (2) (17) (12) (5) C (2) (18) (13) (5) H * C (3) (2) (14) (7) H * C (3) (2) (14) (7) sup-4
6 H * C (2) (2) (13) (6) H * C (2) (18) (12) (5) H * C (2) (17) (13) (5) H51A * H51B * H51C * C (2) (18) (13) (5) H52A * H52B * H52C * Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 S (3) (3) (3) (2) (2) (2) S (3) (3) (3) (2) (2) (2) S (3) (3) (3) (2) (2) (2) S (3) (3) (3) (2) (2) (2) N (10) (10) (10) (8) (8) (8) N (10) (10) (9) (8) (7) (7) N (9) (9) (9) (7) (7) (7) N (10) (10) (10) (8) (8) (8) N (10) (10) (9) (8) (7) (8) N (9) (9) (9) (7) (7) (7) O (9) (8) (8) (7) (7) (7) O (8) (8) (8) (6) (6) (6) O (9) (8) (9) (7) (7) (7) O (8) (8) (8) (6) (6) (6) C (11) (12) (13) (9) (10) (10) C (14) (13) (15) (11) (12) (11) C (16) (15) (15) (12) (12) (12) C (14) (14) (19) (11) (13) (13) C (14) (13) (19) (11) (13) (12) C (13) (13) (15) (10) (11) (11) C (12) (12) (13) (9) (10) (10) C (11) (11) (11) (9) (9) (9) C (11) (11) (11) (9) (9) (9) C (11) (11) (10) (9) (8) (8) C (11) (11) (11) (9) (9) (9) C (11) (11) (11) (9) (9) (9) C (11) (11) (11) (9) (8) (9) C (11) (11) (11) (9) (8) (8) C (11) (11) (11) (8) (8) (8) C (11) (11) (11) (9) (8) (8) C (12) (12) (11) (9) (9) (9) sup-5
7 C (11) (11) (11) (9) (8) (8) C (11) (11) (11) (9) (9) (9) C (12) (12) (12) (9) (9) (10) C (13) (14) (12) (11) (10) (10) C (14) (14) (12) (11) (10) (10) C (12) (12) (13) (10) (10) (10) C (12) (12) (11) (9) (9) (9) C (13) (12) (13) (10) (10) (10) C (11) (12) (12) (9) (9) (9) C (12) (12) (13) (10) (10) (10) C (2) (16) (18) (15) (16) (13) C (3) (19) (2) (18) (2) (16) C (16) (14) (19) (12) (14) (13) C (15) (14) (17) (12) (13) (12) C (14) (14) (14) (11) (11) (11) C (12) (12) (13) (9) (10) (10) C (12) (12) (11) (9) (9) (9) C (11) (11) (11) (9) (9) (9) C (12) (11) (11) (9) (9) (9) C (12) (11) (12) (9) (9) (9) C (11) (11) (12) (9) (9) (9) C (11) (11) (11) (9) (8) (9) C (11) (11) (11) (8) (8) (8) C (11) (10) (11) (8) (8) (8) C (11) (11) (11) (9) (9) (9) C (12) (12) (12) (9) (9) (9) C (11) (10) (11) (8) (8) (8) C (11) (12) (11) (9) (9) (9) C (14) (13) (12) (11) (10) (10) C (18) (14) (15) (13) (13) (11) C (16) (16) (14) (13) (12) (12) C (13) (14) (12) (11) (10) (10) C (12) (12) (12) (9) (9) (9) C (13) (12) (13) (10) (10) (10) C (11) (12) (13) (9) (9) (10) Geometric parameters (Å, º) S1 C (2) C20 H S1 C (2) C21 C (3) S2 C (2) C21 H S3 C (2) C22 C (3) S3 C (2) C22 H S4 C (2) C23 C (3) N1 C (3) C23 H N1 N (2) C24 H N1 H C25 H25A N2 C (3) C25 H25B sup-6
8 N3 C (3) C25 H25C N3 C (3) C26 H26A N3 H C26 H26B N4 C (3) C26 H26C N4 N (2) C27 C (3) N4 H C27 C (3) N5 C (3) C27 C (3) N6 C (3) C28 C (4) N6 C (3) C28 H N6 H C29 C (4) O1 C (2) C29 H O1 C (3) C30 C (4) O2 C (2) C30 H O2 C (2) C31 C (3) O3 C (3) C31 H O3 C (3) C32 H O4 C (2) C33 H33A O4 C (3) C33 H33B C1 C (3) C35 C (3) C1 C (3) C35 C (3) C1 C (3) C35 C (3) C2 C (3) C36 H C2 H C37 C (3) C3 C (4) C38 C (3) C3 H3A C38 H C4 C (4) C39 C (3) C4 H4A C40 C (3) C5 C (3) C40 C (3) C5 H C42 C (3) C6 H6A C42 C (3) C7 H7A C43 H43A C7 H7B C43 H43B C9 C (3) C43 H43C C9 H C44 C (3) C10 C (3) C45 C (3) C10 C (3) C45 C (3) C11 C (3) C46 C (3) C12 C (3) C46 H C12 H C47 C (4) C13 C (3) C47 H C14 C (3) C48 C (4) C14 C (3) C48 H C16 C (3) C49 C (3) C16 C (3) C49 H C17 H17A C50 H C17 H17B C51 H51A C17 H17C C51 H51B C18 C (3) C51 H51C sup-7
9 C19 C (3) C52 H52A C19 C (3) C52 H52B C20 C (3) C52 H52C C8 S1 C (10) H25A C25 H25B C34 S3 C (11) O1 C25 H25C C8 N1 N (17) H25A C25 H25C C8 N1 H H25B C25 H25C N2 N1 H O2 C26 H26A C9 N2 N (18) O2 C26 H26B C15 N3 C (17) H26A C26 H26B C15 N3 H O2 C26 H26C C16 N3 H H26A C26 H26C C34 N4 N (18) H26B C26 H26C C34 N4 H C28 C27 C (2) N5 N4 H C28 C27 C (2) C36 N5 N (18) C32 C27 C (2) C41 N6 C (17) C27 C28 C (3) C41 N6 H C27 C28 H C42 N6 H C29 C28 H C11 O1 C (17) C30 C29 C (3) C13 O2 C (17) C30 C29 H C37 O3 C (17) C28 C29 H C39 O4 C (17) C29 C30 C (3) C6 C1 C (2) C29 C30 H C6 C1 C (2) C31 C30 H C2 C1 C (2) C30 C31 C (2) C3 C2 C (2) C30 C31 H C3 C2 H C32 C31 H C1 C2 H C31 C32 C (2) C2 C3 C (3) C31 C32 H C2 C3 H3A C27 C32 H C4 C3 H3A C27 C33 S (15) C5 C4 C (2) C27 C33 H33A C5 C4 H4A S3 C33 H33A C3 C4 H4A C27 C33 H33B C4 C5 C (2) S3 C33 H33B C4 C5 H H33A C33 H33B C6 C5 H N4 C34 S (17) C1 C6 C (2) N4 C34 S (16) C1 C6 H6A S4 C34 S (14) C5 C6 H6A C37 C35 C (19) C1 C7 S (15) C37 C35 C (19) C1 C7 H7A C41 C35 C (2) S1 C7 H7A N5 C36 C (2) C1 C7 H7B N5 C36 H S1 C7 H7B C35 C36 H H7A C7 H7B O3 C37 C (2) sup-8
10 N1 C8 S (16) O3 C37 C (19) N1 C8 S (15) C38 C37 C (2) S2 C8 S (13) C39 C38 C (2) N2 C9 C (19) C39 C38 H N2 C9 H C37 C38 H C10 C9 H O4 C39 C (19) C11 C10 C (19) O4 C39 C (18) C11 C10 C (19) C38 C39 C (19) C15 C10 C (19) C39 C40 C (19) O1 C11 C (19) C39 C40 C (19) O1 C11 C (18) C41 C40 C (18) C12 C11 C (2) N6 C41 C (18) C13 C12 C (2) N6 C41 C (19) C13 C12 H C40 C41 C (19) C11 C12 H C44 C42 N (19) O2 C13 C (19) C44 C42 C (2) O2 C13 C (19) N6 C42 C (18) C12 C13 C (19) C42 C43 H43A C13 C14 C (19) C42 C43 H43B C13 C14 C (2) H43A C43 H43B C15 C14 C (18) C42 C43 H43C N3 C15 C (18) H43A C43 H43C N3 C15 C (19) H43B C43 H43C C14 C15 C (19) C42 C44 C (18) C18 C16 N (18) C42 C44 C (2) C18 C16 C (19) C40 C44 C (19) N3 C16 C (18) C46 C45 C (2) C16 C17 H17A C46 C45 C (2) C16 C17 H17B C50 C45 C (2) H17A C17 H17B C47 C46 C (2) C16 C17 H17C C47 C46 H H17A C17 H17C C45 C46 H H17B C17 H17C C48 C47 C (2) C16 C18 C (18) C48 C47 H C16 C18 C (19) C46 C47 H C14 C18 C (2) C47 C48 C (2) C24 C19 C (2) C47 C48 H C24 C19 C (2) C49 C48 H C20 C19 C (2) C50 C49 C (2) C21 C20 C (2) C50 C49 H C21 C20 H C48 C49 H C19 C20 H C49 C50 C (2) C22 C21 C (2) C49 C50 H C22 C21 H C45 C50 H C20 C21 H O3 C51 H51A C23 C22 C (2) O3 C51 H51B C23 C22 H H51A C51 H51B C21 C22 H O3 C51 H51C sup-9
11 C24 C23 C (2) H51A C51 H51C C24 C23 H H51B C51 H51C C22 C23 H O4 C52 H52A C23 C24 C (2) O4 C52 H52B C23 C24 H H52A C52 H52B C19 C24 H O4 C52 H52C O1 C25 H25A H52A C52 H52C O1 C25 H25B H52B C52 H52C C8 N1 N2 C (2) C18 C19 C24 C (2) C34 N4 N5 C (2) C32 C27 C28 C (5) C6 C1 C2 C3 0.3 (4) C33 C27 C28 C (3) C7 C1 C2 C (2) C27 C28 C29 C (5) C1 C2 C3 C4 0.8 (4) C28 C29 C30 C (5) C2 C3 C4 C5 1.3 (4) C29 C30 C31 C (4) C3 C4 C5 C6 0.6 (4) C30 C31 C32 C (4) C2 C1 C6 C5 1.0 (4) C28 C27 C32 C (4) C7 C1 C6 C (2) C33 C27 C32 C (2) C4 C5 C6 C1 0.5 (4) C28 C27 C33 S (3) C6 C1 C7 S (2) C32 C27 C33 S (2) C2 C1 C7 S (3) C34 S3 C33 C (16) C8 S1 C7 C (16) N5 N4 C34 S (15) N2 N1 C8 S (15) N5 N4 C34 S3 4.9 (3) N2 N1 C8 S1 5.2 (2) C33 S3 C34 N (17) C7 S1 C8 N (16) C33 S3 C34 S (18) C7 S1 C8 S (18) N4 N5 C36 C (18) N1 N2 C9 C (18) C37 C35 C36 N (2) N2 C9 C10 C (2) C41 C35 C36 N5 1.9 (3) N2 C9 C10 C (3) C51 O3 C37 C (3) C25 O1 C11 C (3) C51 O3 C37 C (19) C25 O1 C11 C (19) C41 C35 C37 O (18) C15 C10 C11 O (18) C36 C35 C37 O3 1.4 (3) C9 C10 C11 O1 5.1 (3) C41 C35 C37 C (3) C15 C10 C11 C (3) C36 C35 C37 C (2) C9 C10 C11 C (2) O3 C37 C38 C (2) O1 C11 C12 C (2) C35 C37 C38 C (3) C10 C11 C12 C (3) C52 O4 C39 C (3) C26 O2 C13 C (3) C52 O4 C39 C (18) C26 O2 C13 C (18) C37 C38 C39 O (19) C11 C12 C13 O (19) C37 C38 C39 C (3) C11 C12 C13 C (3) O4 C39 C40 C (18) O2 C13 C14 C (18) C38 C39 C40 C (3) C12 C13 C14 C (3) O4 C39 C40 C (4) O2 C13 C14 C (4) C38 C39 C40 C (2) C12 C13 C14 C (2) C42 N6 C41 C (2) C16 N3 C15 C (2) C42 N6 C41 C (2) C16 N3 C15 C (2) C39 C40 C41 N (18) C13 C14 C15 N (18) C44 C40 C41 N6 0.5 (2) sup-10
12 C18 C14 C15 N3 2.2 (2) C39 C40 C41 C (3) C13 C14 C15 C (3) C44 C40 C41 C (2) C18 C14 C15 C (19) C37 C35 C41 N (2) C11 C10 C15 N (2) C36 C35 C41 N6 2.6 (3) C9 C10 C15 N3 2.0 (3) C37 C35 C41 C (3) C11 C10 C15 C (3) C36 C35 C41 C (2) C9 C10 C15 C (2) C41 N6 C42 C (2) C15 N3 C16 C (2) C41 N6 C42 C (19) C15 N3 C16 C (19) N6 C42 C44 C (2) N3 C16 C18 C (2) C43 C42 C44 C (2) C17 C16 C18 C (2) N6 C42 C44 C (19) N3 C16 C18 C (19) C43 C42 C44 C (4) C17 C16 C18 C (4) C39 C40 C44 C (2) C13 C14 C18 C (2) C41 C40 C44 C (2) C15 C14 C18 C (2) C39 C40 C44 C (4) C13 C14 C18 C (4) C41 C40 C44 C (2) C15 C14 C18 C (2) C42 C44 C45 C (3) C16 C18 C19 C (2) C40 C44 C45 C (2) C14 C18 C19 C (3) C42 C44 C45 C (2) C16 C18 C19 C (3) C40 C44 C45 C (3) C14 C18 C19 C (2) C50 C45 C46 C (4) C24 C19 C20 C (3) C44 C45 C46 C (2) C18 C19 C20 C (2) C45 C46 C47 C (4) C19 C20 C21 C (4) C46 C47 C48 C (4) C20 C21 C22 C (4) C47 C48 C49 C (4) C21 C22 C23 C (4) C48 C49 C50 C (4) C22 C23 C24 C (3) C46 C45 C50 C (3) C20 C19 C24 C (3) C44 C45 C50 C (2) Hydrogen-bond geometry (Å, º) D H A D H H A D A D H A N1 H1 S (2) 164 N4 H4 S (2) 170 sup-11
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